Saredutant

Base Information

• Chemical Name: Saredutant
• CAS No.: 142001-63-6
• Molecular Formula: C₃₁H₃₅Cl₂N₃O₂
• Molecular Weight: 552.544
• UNII: 720U2QK8I5
• DSSTox Substance ID: DTXSID00161923
• Nikkaji Number: J462.751B
• Wikipedia: Saredutant
• Wikidata: Q3473757
• NCI Thesaurus Code: C152301
• Pharos Ligand ID: UL4D4K8T286C
• Metabolomics Workbench ID: 149887
• ChEMBL ID: CHEMBL308148
• Mol file: 142001-63-6.mol

Synonyms:(S)-N-methyl-N(4-(4-acetylamino-4-phenylpiperidino)-2-(3,4-dichlorophenyl)butyl)benzamide;saredutant;SR 48965;SR 48968;SR 48968C;SR-48968;SR-48968C;SR48968;SR48968C

Chemical Property of Saredutant

Chemical Property:

• Vapor Pressure: 1.91E-21mmHg at 25°C
• Boiling Point: 734.7°Cat760mmHg
• PKA: 15.88±0.20(Predicted)
• Flash Point: 398.1°C
• PSA: 52.65000
• Density: 1.26g/cm³
• LogP: 6.69550
• XLogP3: 5.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 9
• Exact Mass: 551.2106328
• Heavy Atom Count: 38
• Complexity: 760

Purity/Quality:

99% ^*data from raw suppliers

Saredutant 99.30% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1(CCN(CC1)CCC(CN(C)C(=O)C2=CC=CC=C2)C3=CC(=C(C=C3)Cl)Cl)C4=CC=CC=C4
• Isomeric SMILES: CC(=O)NC1(CCN(CC1)CC[C@H](CN(C)C(=O)C2=CC=CC=C2)C3=CC(=C(C=C3)Cl)Cl)C4=CC=CC=C4
• Recent ClinicalTrials: An Eight-week Study of Saredutant and Paroxetine as Combination Treatment for Major Depressive Disorder
• Recent EU Clinical Trials: an eight-week, multicenter, double-blind, placebo-controlled study evaluating the efficacy, safety and tolerability of one fixed 100 mg dose of Saredutant in patients with Major Depressive Disorder

Technology Process of Saredutant

There total 8 articles about Saredutant which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(2E)-but-2-enedioic acid (110-17-8,26099-09-2) + N-(4-phenylpiperidin-4-yl)acetamide (146396-04-5) → SR 48212A (142001-63-6,159125-41-4)

Guidance literature:

With hydrogenchloride; sodium hydroxide; In dichloromethane; water; potassium carbonate; acetone; acetonitrile;

Reference yield:

3,4-dichloro-benzeneacetonitrile (3218-49-3) → SR 48212A (142001-63-6,159125-41-4)

Guidance literature:

Multi-step reaction with 6 steps

1: NaH / dimethylformamide

2: H₂ / Raney nickel / acidic solution

3: BH₃ / tetrahydrofuran

4: NEt₃ / CH₂Cl₂ / 20 °C

5: NEt₃ / CH₂Cl₂

6: K₂CO₃ / dimethylformamide

With borane; hydrogen; sodium hydride; potassium carbonate; triethylamine; nickel; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(03)00343-3

Reference yield:

α-[2-(Tetrahydropyran-2-yloxy)ethyl]-3,4-dichlorophenyl-acetonitrile (135936-16-2) → SR 48212A (142001-63-6,159125-41-4)

Guidance literature:

Multi-step reaction with 5 steps

1: H₂ / Raney nickel / acidic solution

2: BH₃ / tetrahydrofuran

3: NEt₃ / CH₂Cl₂ / 20 °C

4: NEt₃ / CH₂Cl₂

5: K₂CO₃ / dimethylformamide

With borane; hydrogen; potassium carbonate; triethylamine; nickel; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(03)00343-3

upstream raw materials:

N-(4-phenylpiperidin-4-yl)acetamide

N-[2-(3,4-dichlorophenyl)-3-formylpropyl]-N-methylbenzamide

N-[2-(3,4-dichlorophenyl)-4-[(methylsulfonyl)oxy]butyl]-N-methyl benzamide

3,4-dichloro-benzeneacetonitrile

Refernces

• 1、 Jacobs, Robert T.,Shenvi, Ashok B.,Mauger, Russell C.,Ulatowski, Terrance G.,Aharony, David,Buckner, Carl K.. "4-Alkylpiperidines related to SR-48968: Potent antagonists of the neurokinin-2 (NK2) receptor". . p. 1935 - 1940. Retrieved 2007/10/03.